(C-meso-N-meso-5,12-Dimethyl-7,14-diphenyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-4,11-diene)nickel(II) bis-[O,O'-bis-(4-methyl-phen-yl) dithio-phosphate].

The title complex, [Ni(C(24)H(32)N(4))](C(14)H(14)O(2)PS(2))(2), comprises a centrosymmetric [Ni(meso-diphen-yl[14]dien)](2+) dication (meso-diphen-yl[14]dien is C-meso-N-meso-5,12-dimethyl-7,14-diphenyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-4,11-diene) and two O,O'-bis-(4-methyl-phen-yl) dithio-phosphate anions. The Ni(II) ion lies on an inversion center and is chelated by a tetra-amine macrocycle ligand in a slightly distorted NiN(4) square-planar geometry. Two S atoms from symmetry-related anions are located in pseudo-axial positions with respect to the Ni(II) ion, with Ni⋯S distances of 3.1869 (8) Å. In the crystal, bifurcated inter-molecular N-H⋯S(S) hydrogen bonds connect cations and pairs of anions into three-component clusters. Weak inter-molecular C-H⋯S hydrogen bonds link these clusters into chains along [100].

Related literature

For the synthesis of the tetra­mine macrocyclic ligand, see: n class="Disease">Curtis (2001) ▶. For general background to tetra­mine macrocycles, see: Aoki & Kimura (2002 ▶); For transition metal complexes with O,O′-dialkyl­dithio­phosphate ligands, see: Drew et al. (1987 ▶); Liaw et al. (2005 ▶); Zou et al. (2009 ▶). For the synthesis and crystal structures of related macrocyclic nickel and copper complexes, see: Feng et al. (2009 ▶); He et al. (2010 ▶); Xie et al. (2009 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ni(C24H32N4)](C14H14O2PS2)2

M = 1053.93

Monoclinic,

a = 10.04828 (18) Å

b = 19.6896 (4) Å

c = 13.5112 (3) Å

β = 106.900 (2)°

V = 2557.69 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.65 mm−1

T = 150 K

0.22 × 0.18 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.930, T max = 1

11501 measured reflections

5232 independent reflections

4326 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.085

S = 1.01

5232 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO n class="Disease">RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004849X/lh5160sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004849X/lh5160Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C24H32N4)](C14H14O2PS2)2	F(000) = 1108
Mr = 1053.93	Dx = 1.368 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 5452 reflections
a = 10.04828 (18) Å	θ = 3.0–29.2°
b = 19.6896 (4) Å	µ = 0.65 mm−1
c = 13.5112 (3) Å	T = 150 K
β = 106.900 (2)°	Block, pale-violet
V = 2557.69 (9) Å3	0.22 × 0.18 × 0.16 mm
Z = 2

Oxford Diffraction Xcalibur Eos diffractometer	5232 independent reflections
Radiation source: fine-focus sealed tube	4326 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	k = −24→22
Tmin = 0.930, Tmax = 1.0	l = −16→16
11501 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.033P)2 + 1.139P] where P = (Fo2 + 2Fc2)/3
5232 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.0000	0.5000	0.01821 (10)
N2	0.65018 (15)	0.05440 (8)	0.58612 (13)	0.0187 (4)
H2	0.6883	0.0785	0.5417	0.022*
N1	0.36007 (16)	0.06810 (8)	0.49274 (12)	0.0194 (4)
C7	0.7393 (2)	0.14121 (10)	0.72455 (16)	0.0231 (4)
C3	0.6128 (2)	0.10500 (10)	0.65498 (16)	0.0230 (4)
H3	0.5655	0.0804	0.7001	0.028*
C12	0.8221 (2)	0.18311 (11)	0.68330 (17)	0.0273 (5)
H12	0.8003	0.1886	0.6105	0.033*
C1	0.37339 (19)	0.12907 (10)	0.52677 (16)	0.0215 (4)
C4	0.22025 (19)	0.04534 (10)	0.42970 (17)	0.0257 (5)
H4A	0.1666	0.0842	0.3917	0.031*
H4B	0.1683	0.0256	0.4748	0.031*
C6	0.7588 (2)	0.00694 (10)	0.64466 (16)	0.0248 (5)
H6A	0.7291	−0.0150	0.7007	0.030*
H6B	0.8467	0.0317	0.6761	0.030*
C2	0.5110 (2)	0.15594 (11)	0.59068 (18)	0.0301 (5)
H2B	0.4934	0.1910	0.6379	0.036*
H2A	0.5562	0.1788	0.5437	0.036*
C5	0.2573 (2)	0.18000 (11)	0.50298 (18)	0.0294 (5)
H5A	0.2449	0.1989	0.4338	0.044*
H5C	0.2801	0.2167	0.5542	0.044*
H5B	0.1711	0.1577	0.5054	0.044*
C11	0.9352 (2)	0.21660 (12)	0.74757 (18)	0.0330 (5)
H11	0.9908	0.2450	0.7187	0.040*
C9	0.8874 (2)	0.16789 (13)	0.89515 (18)	0.0382 (6)
H9	0.9094	0.1626	0.9680	0.046*
C8	0.7738 (2)	0.13401 (12)	0.83067 (17)	0.0310 (5)
H8	0.7190	0.1055	0.8600	0.037*
C10	0.9680 (2)	0.20904 (12)	0.85370 (19)	0.0368 (6)
H10	1.0459	0.2322	0.8977	0.044*
P1	0.73840 (5)	0.08481 (3)	0.33089 (4)	0.02337 (13)
S1	0.54518 (6)	0.10019 (3)	0.32732 (5)	0.03221 (15)
S2	0.88615 (6)	0.11448 (3)	0.45192 (4)	0.03143 (14)
O2	0.75506 (14)	0.11660 (7)	0.22395 (11)	0.0274 (3)
O1	0.77128 (15)	0.00483 (7)	0.31873 (11)	0.0272 (3)
C20	0.8809 (2)	0.11224 (11)	0.19887 (16)	0.0255 (5)
C23	1.1212 (2)	0.10828 (13)	0.13572 (17)	0.0332 (6)
C14	0.5849 (2)	−0.02229 (11)	0.16048 (17)	0.0286 (5)
H14	0.5515	0.0231	0.1527	0.034*
C13	0.6975 (2)	−0.04031 (11)	0.24365 (17)	0.0261 (5)
C25	0.9101 (2)	0.05523 (12)	0.14963 (17)	0.0306 (5)
H25	0.8484	0.0175	0.1366	0.037*
C17	0.6815 (3)	−0.15446 (12)	0.1808 (2)	0.0385 (6)
H17	0.7156	−0.1997	0.1883	0.046*
C21	0.9712 (2)	0.16664 (11)	0.21960 (17)	0.0304 (5)
H21	0.9519	0.2053	0.2552	0.037*
C16	0.5682 (2)	−0.13849 (12)	0.09778 (19)	0.0349 (6)
C15	0.5220 (2)	−0.07171 (12)	0.08889 (18)	0.0314 (5)
H15	0.4450	−0.0594	0.0320	0.038*
C18	0.7466 (2)	−0.10621 (11)	0.25325 (19)	0.0324 (5)
H18	0.8247	−0.1184	0.3094	0.039*
C22	1.0910 (2)	0.16418 (13)	0.18768 (17)	0.0342 (6)
H22	1.1533	0.2016	0.2018	0.041*
C26	1.2453 (2)	0.10744 (16)	0.0941 (2)	0.0518 (8)
H26B	1.2785	0.0607	0.0935	0.078*
H26C	1.3196	0.1355	0.1382	0.078*
H26A	1.2182	0.1256	0.0235	0.078*
C24	1.0306 (2)	0.05370 (13)	0.11934 (17)	0.0341 (5)
H24	1.0516	0.0141	0.0865	0.041*
C19	0.4963 (3)	−0.19066 (14)	0.0184 (2)	0.0526 (8)
H19A	0.4047	−0.2011	0.0265	0.079*
H19C	0.5525	−0.2322	0.0282	0.079*
H19B	0.4851	−0.1726	−0.0512	0.079*

	U11	U22	U33	U12	U13	U23
Ni1	0.01354 (17)	0.01832 (19)	0.0208 (2)	0.00210 (14)	0.00195 (14)	−0.00173 (15)
N2	0.0153 (8)	0.0185 (8)	0.0218 (9)	0.0012 (7)	0.0042 (7)	0.0012 (7)
N1	0.0160 (8)	0.0202 (9)	0.0208 (9)	0.0003 (7)	0.0037 (7)	0.0022 (7)
C7	0.0198 (10)	0.0246 (11)	0.0238 (11)	0.0035 (8)	0.0043 (8)	−0.0058 (9)
C3	0.0199 (10)	0.0281 (11)	0.0219 (11)	−0.0018 (9)	0.0074 (8)	−0.0063 (9)
C12	0.0248 (10)	0.0302 (12)	0.0257 (12)	0.0012 (9)	0.0052 (9)	−0.0035 (10)
C1	0.0192 (10)	0.0217 (11)	0.0238 (11)	0.0028 (8)	0.0068 (8)	0.0009 (9)
C4	0.0142 (9)	0.0213 (11)	0.0369 (13)	0.0017 (8)	−0.0001 (9)	0.0005 (10)
C6	0.0201 (10)	0.0213 (11)	0.0267 (12)	0.0029 (8)	−0.0030 (8)	0.0037 (9)
C2	0.0204 (10)	0.0256 (12)	0.0405 (14)	0.0028 (9)	0.0029 (9)	−0.0102 (10)
C5	0.0230 (10)	0.0204 (11)	0.0416 (14)	0.0046 (9)	0.0044 (9)	−0.0028 (10)
C11	0.0265 (11)	0.0286 (13)	0.0429 (15)	−0.0019 (10)	0.0088 (10)	−0.0077 (11)
C9	0.0380 (13)	0.0442 (15)	0.0259 (13)	0.0053 (11)	−0.0009 (10)	−0.0084 (11)
C8	0.0302 (12)	0.0359 (13)	0.0263 (12)	0.0012 (10)	0.0072 (9)	−0.0027 (10)
C10	0.0262 (11)	0.0359 (13)	0.0399 (15)	0.0000 (10)	−0.0036 (10)	−0.0142 (12)
P1	0.0218 (3)	0.0267 (3)	0.0235 (3)	0.0008 (2)	0.0095 (2)	0.0013 (2)
S1	0.0223 (3)	0.0446 (4)	0.0323 (3)	0.0051 (2)	0.0119 (2)	0.0032 (3)
S2	0.0263 (3)	0.0397 (3)	0.0285 (3)	−0.0055 (2)	0.0084 (2)	−0.0055 (3)
O2	0.0245 (7)	0.0321 (8)	0.0281 (8)	0.0041 (6)	0.0117 (6)	0.0071 (7)
O1	0.0287 (8)	0.0258 (8)	0.0256 (8)	0.0026 (6)	0.0055 (6)	0.0008 (7)
C20	0.0226 (10)	0.0339 (12)	0.0215 (11)	0.0019 (9)	0.0088 (8)	0.0068 (10)
C23	0.0220 (11)	0.0558 (16)	0.0203 (11)	0.0021 (11)	0.0037 (9)	0.0110 (11)
C14	0.0326 (12)	0.0261 (11)	0.0283 (12)	−0.0017 (10)	0.0109 (10)	0.0045 (10)
C13	0.0288 (11)	0.0278 (12)	0.0255 (12)	−0.0030 (9)	0.0138 (9)	0.0012 (10)
C25	0.0308 (12)	0.0367 (13)	0.0259 (12)	−0.0037 (10)	0.0107 (9)	−0.0001 (10)
C17	0.0433 (14)	0.0233 (12)	0.0577 (17)	−0.0031 (11)	0.0284 (13)	0.0003 (12)
C21	0.0329 (12)	0.0280 (12)	0.0303 (13)	0.0003 (10)	0.0091 (10)	0.0058 (10)
C16	0.0395 (13)	0.0307 (13)	0.0425 (15)	−0.0141 (11)	0.0247 (12)	−0.0050 (11)
C15	0.0316 (12)	0.0356 (13)	0.0286 (12)	−0.0094 (10)	0.0113 (10)	0.0009 (11)
C18	0.0335 (12)	0.0282 (12)	0.0390 (14)	0.0019 (10)	0.0160 (10)	0.0043 (11)
C22	0.0282 (11)	0.0421 (14)	0.0301 (13)	−0.0079 (11)	0.0052 (10)	0.0121 (11)
C26	0.0261 (12)	0.092 (2)	0.0389 (15)	0.0024 (14)	0.0126 (11)	0.0119 (15)
C24	0.0343 (12)	0.0459 (15)	0.0236 (12)	0.0058 (11)	0.0107 (10)	−0.0011 (11)
C19	0.0566 (17)	0.0418 (16)	0.066 (2)	−0.0235 (13)	0.0277 (15)	−0.0154 (14)

Ni1—N2	1.9385 (15)	C10—H10	0.9500
Ni1—N2i	1.9385 (15)	P1—S1	1.9517 (7)
Ni1—N1	1.9247 (16)	P1—S2	1.9514 (8)
Ni1—N1i	1.9247 (16)	P1—O2	1.6273 (15)
N2—H2	0.9300	P1—O1	1.6271 (15)
N2—C3	1.484 (2)	O2—C20	1.403 (2)
N2—C6	1.479 (2)	O1—C13	1.390 (3)
N1—C1	1.279 (3)	C20—C25	1.379 (3)
N1—C4	1.485 (2)	C20—C21	1.379 (3)
C7—C3	1.521 (3)	C23—C22	1.386 (3)
C7—C12	1.397 (3)	C23—C26	1.510 (3)
C7—C8	1.381 (3)	C23—C24	1.384 (3)
C3—H3	1.0000	C14—H14	0.9500
C3—C2	1.513 (3)	C14—C13	1.389 (3)
C12—H12	0.9500	C14—C15	1.388 (3)
C12—C11	1.381 (3)	C13—C18	1.381 (3)
C1—C2	1.498 (3)	C25—H25	0.9500
C1—C5	1.500 (3)	C25—C24	1.387 (3)
C4—H4A	0.9900	C17—H17	0.9500
C4—H4B	0.9900	C17—C16	1.382 (3)
C4—C6i	1.495 (3)	C17—C18	1.385 (3)
C6—C4i	1.495 (3)	C21—H21	0.9500
C6—H6A	0.9900	C21—C22	1.393 (3)
C6—H6B	0.9900	C16—C15	1.388 (3)
C2—H2B	0.9900	C16—C19	1.509 (3)
C2—H2A	0.9900	C15—H15	0.9500
C5—H5A	0.9800	C18—H18	0.9500
C5—H5C	0.9800	C22—H22	0.9500
C5—H5B	0.9800	C26—H26B	0.9800
C11—H11	0.9500	C26—H26C	0.9800
C11—C10	1.383 (3)	C26—H26A	0.9800
C9—H9	0.9500	C24—H24	0.9500
C9—C8	1.389 (3)	C19—H19A	0.9800
C9—C10	1.375 (3)	C19—H19C	0.9800
C8—H8	0.9500	C19—H19B	0.9800
Ni1—N2—H2	106.8	C8—C7—C12	118.43 (19)
N2i—Ni1—N2	180	C8—C9—H9	119.9
N2—C3—C7	112.54 (15)	C10—C11—H11	119.8
N2—C3—H3	108.0	C10—C9—H9	119.9
N2—C3—C2	109.70 (16)	C10—C9—C8	120.1 (2)
N2—C6—C4i	107.56 (16)	S2—P1—S1	118.90 (4)
N2—C6—H6A	110.2	O2—P1—S1	106.07 (6)
N2—C6—H6B	110.2	O2—P1—S2	112.29 (6)
N1—Ni1—N2	94.32 (7)	O1—P1—S1	112.17 (6)
N1—Ni1—N2i	85.68 (7)	O1—P1—S2	104.30 (6)
N1i—Ni1—N2	85.68 (7)	O1—P1—O2	101.90 (8)
N1i—Ni1—N2i	94.32 (7)	C20—O2—P1	121.56 (13)
N1i—Ni1—N1	180	C20—C25—H25	120.4
N1—C1—C2	121.44 (17)	C20—C25—C24	119.1 (2)
N1—C1—C5	123.84 (18)	C20—C21—H21	120.4
N1—C4—H4A	110.2	C20—C21—C22	119.2 (2)
N1—C4—H4B	110.2	C23—C22—C21	121.4 (2)
N1—C4—C6i	107.38 (16)	C23—C22—H22	119.3
C7—C3—H3	108.0	C23—C26—H26B	109.5
C7—C12—H12	119.7	C23—C26—H26C	109.5
C7—C8—C9	121.0 (2)	C23—C26—H26A	109.5
C7—C8—H8	119.5	C23—C24—C25	121.8 (2)
C3—N2—Ni1	116.89 (11)	C23—C24—H24	119.1
C3—N2—H2	106.8	C14—C13—O1	124.28 (19)
C3—C2—H2B	108.1	C14—C15—H15	119.0
C3—C2—H2A	108.1	C13—O1—P1	127.73 (13)
C12—C7—C3	121.19 (18)	C13—C14—H14	120.5
C12—C11—H11	119.8	C13—C18—C17	119.7 (2)
C12—C11—C10	120.3 (2)	C13—C18—H18	120.1
C1—N1—Ni1	129.59 (14)	C25—C20—O2	119.94 (19)
C1—N1—C4	118.19 (16)	C25—C24—H24	119.1
C1—C2—C3	116.97 (17)	C17—C16—C15	117.5 (2)
C1—C2—H2B	108.1	C17—C16—C19	122.2 (2)
C1—C2—H2A	108.1	C17—C18—H18	120.1
C1—C5—H5A	109.5	C21—C20—O2	119.30 (19)
C1—C5—H5C	109.5	C21—C20—C25	120.69 (19)
C1—C5—H5B	109.5	C21—C22—H22	119.3
C4—N1—Ni1	111.99 (12)	C16—C17—H17	119.1
C4i—C6—H6A	110.2	C16—C17—C18	121.8 (2)
C4i—C6—H6B	110.2	C16—C15—C14	122.1 (2)
H4A—C4—H4B	108.5	C16—C15—H15	119.0
C6—N2—Ni1	107.25 (12)	C16—C19—H19A	109.5
C6—N2—H2	106.8	C16—C19—H19C	109.5
C6—N2—C3	111.77 (15)	C16—C19—H19B	109.5
C6i—C4—H4A	110.2	C15—C14—H14	120.5
C6i—C4—H4B	110.2	C15—C14—C13	118.9 (2)
H6A—C6—H6B	108.5	C15—C16—C19	120.3 (2)
C2—C3—C7	110.38 (16)	C18—C13—O1	115.63 (19)
C2—C3—H3	108.0	C18—C13—C14	120.0 (2)
C2—C1—C5	114.66 (17)	C18—C17—H17	119.1
H2B—C2—H2A	107.3	C22—C23—C26	121.6 (2)
H5A—C5—H5C	109.5	C22—C21—H21	120.4
H5A—C5—H5B	109.5	H26B—C26—H26C	109.5
H5C—C5—H5B	109.5	H26B—C26—H26A	109.5
C11—C12—C7	120.5 (2)	H26C—C26—H26A	109.5
C11—C12—H12	119.7	C24—C23—C22	117.8 (2)
C11—C10—H10	120.2	C24—C23—C26	120.5 (2)
C9—C8—H8	119.5	C24—C25—H25	120.4
C9—C10—C11	119.7 (2)	H19A—C19—H19C	109.5
C9—C10—H10	120.2	H19A—C19—H19B	109.5
C8—C7—C3	120.38 (19)	H19C—C19—H19B	109.5
Ni1—N2—C3—C7	175.86 (13)	C8—C7—C12—C11	−0.2 (3)
Ni1—N2—C3—C2	−60.84 (19)	C8—C9—C10—C11	0.1 (4)
Ni1—N2—C6—C4i	45.69 (18)	C10—C9—C8—C7	−0.4 (3)
Ni1—N1—C1—C2	−6.0 (3)	P1—O2—C20—C25	85.7 (2)
Ni1—N1—C1—C5	171.17 (15)	P1—O2—C20—C21	−97.2 (2)
Ni1—N1—C4—C6i	−25.2 (2)	P1—O1—C13—C14	4.3 (3)
N2i—Ni1—N1—C1	−174.21 (19)	P1—O1—C13—C18	−178.36 (15)
N2—Ni1—N1—C1	5.79 (19)	S1—P1—O2—C20	−177.67 (14)
N2—Ni1—N1—C4	180.00 (13)	S1—P1—O1—C13	50.57 (17)
N2i—Ni1—N1—C4	0.00 (13)	S2—P1—O2—C20	50.91 (16)
N2—C3—C2—C1	62.2 (2)	S2—P1—O1—C13	−179.45 (15)
N1—Ni1—N2—C3	28.14 (14)	O2—P1—O1—C13	−62.47 (17)
N1i—Ni1—N2—C3	−151.86 (14)	O2—C20—C25—C24	175.78 (19)
N1—Ni1—N2—C6	154.50 (13)	O2—C20—C21—C22	−175.25 (18)
N1i—Ni1—N2—C6	−25.50 (13)	O1—P1—O2—C20	−60.14 (16)
N1—C1—C2—C3	−28.3 (3)	O1—C13—C18—C17	−178.68 (19)
C7—C3—C2—C1	−173.27 (18)	C20—C25—C24—C23	−1.1 (3)
C7—C12—C11—C10	0.0 (3)	C20—C21—C22—C23	−0.1 (3)
C3—N2—C6—C4i	175.03 (16)	C14—C13—C18—C17	−1.2 (3)
C3—C7—C12—C11	178.85 (18)	C13—C14—C15—C16	0.0 (3)
C3—C7—C8—C9	−178.67 (19)	C25—C20—C21—C22	1.7 (3)
C12—C7—C3—N2	64.4 (2)	C17—C16—C15—C14	−0.7 (3)
C12—C7—C3—C2	−58.5 (2)	C21—C20—C25—C24	−1.2 (3)
C12—C7—C8—C9	0.4 (3)	C16—C17—C18—C13	0.4 (3)
C12—C11—C10—C9	0.1 (3)	C15—C14—C13—O1	178.26 (19)
C1—N1—C4—C6i	149.72 (18)	C15—C14—C13—C18	1.0 (3)
C4—N1—C1—C2	−179.86 (19)	C18—C17—C16—C15	0.5 (3)
C4—N1—C1—C5	−2.7 (3)	C18—C17—C16—C19	−180.0 (2)
C6—N2—C3—C7	51.8 (2)	C22—C23—C24—C25	2.6 (3)
C6—N2—C3—C2	175.07 (16)	C26—C23—C22—C21	175.4 (2)
C5—C1—C2—C3	154.36 (19)	C26—C23—C24—C25	−174.9 (2)
C8—C7—C3—N2	−116.5 (2)	C24—C23—C22—C21	−2.1 (3)
C8—C7—C3—C2	120.6 (2)	C19—C16—C15—C14	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1	0.93	2.87	3.4652 (17)	123
N2—H2···S2	0.93	2.71	3.5789 (17)	156
C5—H5B···S2ii	0.98	2.87	3.815 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1	0.93	2.87	3.4652 (17)	123
N2—H2⋯S2	0.93	2.71	3.5789 (17)	156
C5—H5B⋯S2i	0.98	2.87	3.815 (2)	162

Symmetry code: (i) .